This invention deals with cyclic delocalized cations joined together by spacer groups, with anions of equal number to cations to maintain charge neutrality. These materials are well suited for use as electrolytes, lubricants, solvents for extractions and for running reactions, biphase catalysis media, and immobilizing ionic media for electroluminescent and electrochromic devices.
There has been limited disclosure of compounds containing two or more delocalized cations, and none have disclosed the utility of the compounds as electrolytes, lubricants, solvents, etc.
Acerete et al. (Revue Roumaine de Chimie, 36 (1991) 629) disclose the neutral bisazolyl compounds with one or two methylene spacer groups between the ring structures. They investigated the proton acidity of the neutral compounds.
Claramunt, Elguero, and Meco (J. Heterocyclic Chem., 20 (1983) 1245) disclose the NMR characteristics of bisimidazole compounds with one methylene group as a spacer and the bisimidazolium salts with halides as the counter anion.
Claramunt, Hernandez, et al. (Bull. De la Societe Chemique de France (1983) II-5) disclose the synthesis of bispyrazole compounds with one methylene group as a spacer and the bispyrazolium salts using fluorosulfaonate (FSO3xe2x88x92) as the counter anion.
Ohno, Nakai, and Ito (Chemistry Letters (1998)15) disclose the use of polyethylene oxide linked sulfonamide anions for use as lithium polymer electrolytes. They teach that by mixing these bis-sulfonamide anions with the bromo imidazolium cations having polyethylene oxide side chains the ionic conductivity is improved.
Torres et al. (Bull. Soc. Chim. Belg., 101 (1992) 29) disclose the synthesis and NMR characteristics of the salts resulting from 1,2-bisazolylethanes and 1,2-bisbenzazolylethanes having fluorosulfonate (FSO3xe2x88x92) or sulfate (SO32xe2x88x92) as the counter anions. These biscation materials have high melting points, in some cases well above 300xc2x0 C.
Cabildo et al. (J. Heterocyclic Chem. 34 (1997) 367) disclose the mass spectrometry of bisimidazolium and bispyrazolium salts with one and two methylene spacer groups between the two cations and with halides (iodide, bormide, or chloride) or SO4Hxe2x88x92 as the counter anion. They teach the advantage of using Fast Atom Bombardment in determining the structural information of these salts.
There has been disclosure of divalent imidazolium compounds in general (see e.g. Murphy, Publication WO 00/32658 (application PCT/US99/28740)). However, this publication does not distinguish between the various divalent compounds in terms of thermal and electrochemical stability and phase transition characteristics. In addition, the publication deals with the use of these compounds as components in the polymerization of isoolefins, particularly poly-isobutylenes.
This invention deals with cyclic delocalized cations joined together by spacer groups, with anions of equal number to cations to maintain charge neutrality. These spacer groups may be organic or inorganic in origin and may vary in length. The spacer groups may be saturated, containing single bonds, or may be unsaturated, containing double and triple bonds. With appropriate design these materials can have melting and glass transition temperatures below, around, and above room temperature. The lyophobic character of these materials may be adjusted, providing unique properties.
These materials are well suited for use as electrolytes, lubricants, solvents for extractions and for running reactions, biphase catalysis media, and immobilizing ionic media for electroluminescent and electrochromic devices.